WO2021060240A1 - ７－オキサ－３，４－ジアザビシクロ［４．１．０］ヘプタ－４－エン－２－オン化合物および除草剤 - Google Patents

７－オキサ－３，４－ジアザビシクロ［４．１．０］ヘプタ－４－エン－２－オン化合物および除草剤 Download PDF

Info

Publication number
WO2021060240A1
WO2021060240A1 PCT/JP2020/035689 JP2020035689W WO2021060240A1 WO 2021060240 A1 WO2021060240 A1 WO 2021060240A1 JP 2020035689 W JP2020035689 W JP 2020035689W WO 2021060240 A1 WO2021060240 A1 WO 2021060240A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
substituted
unsubstituted
groups
represented
Prior art date
Application number
PCT/JP2020/035689
Other languages
English (en)
French (fr)
Japanese (ja)
Inventor
健 三原
庸二 池田
ゆきな 瀧
一成 加登
大岡　浩仁
一成 藤井
Original Assignee
日本曹達株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to EP20870221.7A priority Critical patent/EP4035528B1/en
Priority to KR1020227007865A priority patent/KR20220066885A/ko
Priority to MX2022002898A priority patent/MX2022002898A/es
Priority to UAA202200941A priority patent/UA128513C2/uk
Priority to JP2021548911A priority patent/JP7459122B2/ja
Priority to PL20870221.7T priority patent/PL4035528T3/pl
Priority to CA3153862A priority patent/CA3153862A1/en
Priority to CN202080063624.1A priority patent/CN114375292A/zh
Application filed by 日本曹達株式会社 filed Critical 日本曹達株式会社
Priority to AU2020355994A priority patent/AU2020355994A1/en
Priority to ES20870221T priority patent/ES2984558T3/es
Priority to BR112022003616A priority patent/BR112022003616A2/pt
Priority to US17/636,710 priority patent/US20220289758A1/en
Priority to DK20870221.7T priority patent/DK4035528T3/da
Publication of WO2021060240A1 publication Critical patent/WO2021060240A1/ja
Priority to ZA2022/02626A priority patent/ZA202202626B/en

Links

Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/58—1,2-Diazines; Hydrogenated 1,2-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P13/00—Herbicides; Algicides
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P13/00—Herbicides; Algicides
    • A01P13/02—Herbicides; Algicides selective
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00

Definitions

  • the present invention relates to a 7-oxa-3,4-diazabicyclo [4.1.0] hepta-4-en-2-one compound and a herbicide containing the same as an active ingredient.
  • the present application claims priority based on Japanese Patent Application No. 2019-174531 filed in Japan on September 25, 2019, the contents of which are incorporated herein by reference.
  • herbicides may be used to control weeds.
  • Various compounds have been proposed as active ingredients of herbicides.
  • Patent Document 1 discloses a compound represented by the formula (A).
  • Herbicides are required not only to have an excellent weed control effect, but also to have less phytotoxicity on crops, to be less likely to remain in the environment, and to not pollute the environment.
  • the subject of the present invention is a novel 7-oxa-3,4-, which is useful as an active ingredient of a herbicide, which has a reliable weed control effect even at a low dose, has less phytotoxicity to crops, and is highly safe for the environment.
  • R 1 is a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, or Shows a 5- to 6-membered cyclic ether group
  • R 2 represents a substituted or unsubstituted C1 ⁇ 6 alkyl group, a substituted or unsubstituted C2 ⁇ 6 alkenyl group or a substituted or unsubstituted C2 ⁇ 6 alkynyl group
  • R 3 is a hydrogen atom, a substituted or unsubstituted C1 to 6 alkyl group, a substituted or unsubstituted C2 to 6 alkenyl group, a substituted or unsubstituted C
  • R 1 , R 2 , and R 3 are the same as their definitions in claim 1.
  • X is a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a hydroxyl group, a substituted or unsubstituted C1-6 alkoxy.
  • R-S (O) 2- NH-
  • R independently represent a substituted or unsubstituted C1-6 alkyl group or a substituted or unsubstituted C3-6 cycloalkyl group, respectively.
  • R a each independently represent a hydrogen atom, a substituted or unsubstituted C1 ⁇ 6 alkyl group or a substituted or unsubstituted C1 ⁇ 6 alkoxy group
  • R b represents a substituted or unsubstituted C1-6 alkyl group or a substituted or unsubstituted phenyl group
  • R c represents a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group;
  • R and R may be bonded to form a 4- to 6-membered ring together with the nitrogen atom to which they are bonded;
  • R 2 S (O) N-, R and R may be bonded to form a 5- to 6-membered ring together with the sulfur atom to which they are bonded;
  • n represents an integer of 0 to 5, and when n is 2 or more, X may be the same or different, and when n is 2 or more, two Xs thereof are combined to be divalent.
  • Organic groups may be formed.
  • R 1 , R 2 , and R 3 are the same as their definitions in claim 1, where X 1 is a halogeno group, a substituted or unsubstituted C1-6 alkyl group, substituted.
  • an unsubstituted C2 to 6 alkenyl group a substituted or unsubstituted C2 to 6 alkynyl group, a substituted or unsubstituted C1 to 6 alkoxy group, a substituted or unsubstituted C1 to 6 alkylthio group, a substituted or unsubstituted C1 to 6 Alkyl sulfinyl groups, substituted or unsubstituted C1-6 alkylsulfonyl groups, substituted or unsubstituted C3-6 cycloalkyl groups, substituted or unsubstituted phenyl groups, substituted or unsubstituted 5-6-membered heterocyclyl groups, nitro Indicates a group or cyano group; m represents an integer of 0 to 3, and when m is 2 or more, X 1 may be the same or different.
  • Substituents on the C1 to 6 alkyl groups in R 2 are halogeno groups, hydroxyl groups, C1 to 6 alkoxy groups, C1 to 6 alkoxy C1 to 6 alkoxy groups, C1 to 6 haloalkoxy groups, and C1 to 6 alkylthio groups.
  • a method for controlling monocotyledonous and / or dicotyledonous weeds in a useful plant which contains the compound according to any one of [1] to [4], a salt thereof, or the compound.
  • a method comprising the step of applying a herbicide to the weed and / or the plant and / or its location.
  • the 7-oxa-3,4-diazabicyclo [4.1.0] hepta-4-en-2-one compound of the present invention exerts a reliable weed control effect even at a low dose, has less phytotoxicity to crops, and has less phytotoxicity. Since it is highly safe for the environment, it is useful as an active ingredient of herbicides.
  • the herbicide of the present invention can be safely used for controlling weeds in the cultivation of agricultural and horticultural crops.
  • the 7-oxa-3,4-diazabicyclo [4.1.0] hepta-4-en-2-one compound of the present invention (hereinafter, may be referred to as “the compound of the present invention” for simplicity) is of the formula. It is a compound represented by (I) (sometimes referred to as compound (I)) or a salt of compound (I). Compound (I) also includes hydrates, various solvates, polymorphs of crystals, and the like. Compound (I) may have a stereoisomer based on an asymmetric carbon, a double bond, or a tautomer. All such isomers and mixtures thereof are within the technical scope of the present invention.
  • the term "unsubstituted” means that it is only a parent group. When there is no description of "substitution” and only the name of the parent group is described, it means “unsubstituted” unless otherwise specified.
  • substituted means that any hydrogen atom of the parent group is substituted with a group (substituent) having the same or different structure as the mother nucleus. Therefore, a “substituent” is another group attached to a parent group.
  • the substituent may be one or two or more.
  • the two or more substituents may be the same or different.
  • Terms such as "C1 to 6" indicate that the number of carbon atoms of the parent group is 1 to 6 or the like. This number of carbon atoms does not include the number of carbon atoms in the substituent. For example, a butyl group having an ethoxy group as a substituent is classified as a C2 alkoxy C4 alkyl group.
  • the "substituent” is chemically acceptable and is not particularly limited as long as it has the effect of the present invention.
  • the groups that can be “substituents” are illustrated below. C1-6 such as methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl group, n-hexyl group, etc.
  • Alkyl group Vinyl group, 1-propenyl group, 2-propenyl group (allyl group), 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, 2-methyl-2-propenyl group, etc.
  • C2-6 alkenyl groups C2-6 alkynyl groups such as ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group;
  • C3-6 cycloalkyl groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group; Phenyl group, naphthyl group; Phenyl C1-6 alkyl groups such as benzyl group and phenethyl group; 3-6 member heterocyclyl group; 3-6 member heterocyclyl C1-6 alkyl group;
  • Hydroxy group C1-6 alkoxy groups such as methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group; C2-6 alkenyloxy groups such as vinyloxy group, allyloxy group, propenyloxy group, butenyloxy group; C2-6 alkynyloxy groups such as ethynyloxy group and propargyloxy group; Phenoxy group, naphthoxy group; Benzyloxy group, phenethyloxy group; 5- to 6-membered heteroaryloxy groups such as thiazolyloxy groups and pyridyloxy groups; 5- to 6-membered heteroaryl C1 to 6 alkyloxy groups such as thiazolylmethyloxy group and pyridylmethyloxy group;
  • Holmil group C1-6 alkylcarbonyl groups such as acetyl group, propionyl group; Formyloxy group; C1-6 alkylcarbonyloxy groups such as acetyloxy group, propionyloxy group; Benzoyl group; C1-6 alkoxycarbonyl groups such as methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, i-propoxycarbonyl group, n-butoxycarbonyl group, t-butoxycarbonyl group; C1-6 alkoxycarbonyloxy groups such as methoxycarbonyloxy group, ethoxycarbonyloxy group, n-propoxycarbonyloxy group, i-propoxycarbonyloxy group, n-butoxycarbonyloxy group, t-butoxycarbonyloxy group; Carboxyl group;
  • Halogeno groups such as fluoro group, chloro group, bromo group, iod group; C1 to chloromethyl group, chloroethyl group, difluoromethyl group, trifluoromethyl group, 2,2,2-trifluoroethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group, etc.
  • C2-6 haloalkyl groups such as 2-chloro-1-propenyl group, 2-fluoro-1-butenyl group; C2-6 haloalkynyl groups such as 4,4-dichloro-1-butynyl group, 4-fluoro-1-pentynyl group, 5-bromo-2-pentynyl group; C1-6 haloalkoxy groups such as difluoromethoxy group, trifluoromethoxy group, 2,2,2-trifluoroethoxy group, 2,3-dichlorobutoxy group; C2-6 haloalkenyloxy groups such as 2-chloropropenyloxy group, 3-bromobutenyloxy group; C1-6 haloalkylcarbonyl groups such as chloroacetyl group, trifluoroacetyl group, trichloroacetyl group;
  • Amino group C1-6 alkyl-substituted amino groups such as methylamino group, dimethylamino group, diethylamino group; Anilino group, naphthylamino group; Phenyl C1-6 alkylamino groups such as benzylamino group, phenethylamino group; Formylamino group; C1-6 alkylcarbonylamino groups such as acetylamino group, propanoylamino group, butyrylamino group, i-propylcarbonylamino group; C1-6 alkoxycarbonylamino groups such as methoxycarbonylamino group, ethoxycarbonylamino group, n-propoxycarbonylamino group, i-propoxycarbonylamino group; Aminocarbonyl group having an unsubstituted or substituent such as an aminocarbonyl group, a dimethylaminocarbonyl group, a phenylaminocarbony
  • C1-6 alkylthio groups such as methylthio group, ethylthio group, n-propylthio group, i-propylthio group, n-butylthio group, i-butylthio group, s-butylthio group, t-butylthio group; C1-6 haloalkylthio groups such as trifluoromethylthio group, 2,2,2-trifluoroethylthio group; Phenylthio group; 5- to 6-membered heteroarylthio groups such as thiazolylthio groups and pyridylthio groups;
  • C1-6 alkylsulfinyl groups such as methylsulfinyl group, ethylsulfinyl group, t-butylsulfinyl group; C1-6 haloalkylsulfinyl groups such as trifluoromethylsulfinyl groups, 2,2,2-trifluoroethylsulfinyl groups; Phenylsulfinyl group; 5- to 6-membered heteroarylsulfinyl groups such as thiazolylsulfinyl groups, pyridylsulfinyl groups; C1-6 alkylsulfonyl groups such as methylsulfonyl groups, ethylsulfonyl groups, t-butylsulfonyl groups; C1-6 haloalkylsulfonyl groups such as trifluoromethylsulfonyl groups, 2,2,2-trifluoroethylsulfony
  • Tri-C1-6 alkyl-substituted silyl groups such as trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group; Triphenylsilyl group; Pentafluorosulfanil group; Cyan group; Nitro group;
  • any hydrogen atom in the substituent may be substituted with a group having a different structure.
  • the "substituent” in this case include a C1 to 6 alkyl group, a C1 to 6 haloalkyl group, a C1 to 6 alkoxy group, a C1 to 6 haloalkoxy group, a halogeno group, a cyano group, a nitro group and the like.
  • the above-mentioned "3- to 6-membered heterocyclyl group” is a 3-membered ring or 4-membered ring containing 1 to 4 heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom as ring constituent atoms.
  • the heterocyclyl group may be monocyclic or polycyclic.
  • the polycyclic heterocyclyl group may have any of a saturated alicyclic ring, an unsaturated alicyclic ring, and an aromatic ring as long as at least one ring is a heterocyclic ring.
  • Examples of the "3- to 6-membered heterocyclyl group” include a 3- to 6-membered saturated heterocyclyl group, a 5- to 6-membered unsaturated heterocyclyl group, and a 5- to 6-membered heteroaryl group.
  • Examples of the 3- to 6-membered saturated heterocyclyl group include an aziridinyl group, an epoxy group, an azetidinyl group, a pyrrolidinyl group, a tetrahydrofuranyl group, a dioxolanyl group, a tetrahydropyranyl group, a piperidyl group, a piperazinyl group, a morpholinyl group and a dioxanyl group. it can.
  • the 5- to 6-membered unsaturated heterocyclyl group includes a pyrrolinyl group, a dihydrofuranyl group, an imidazolinyl group, a pyrazolinyl group, an oxazolinyl group, an isooxazolinyl group, a thiazolinyl group, an isothiazolinyl group, a dihydropyranyl group and a dihydrooxadinyl group. And so on.
  • Examples of the 5-membered heteroaryl group include a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isooxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group and a tetrazolyl group. Can be done.
  • 6-membered heteroaryl group examples include a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridadinyl group, a triazinyl group and the like.
  • R 1 is a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, or It shows a 5- to 6-membered cyclic ether group.
  • the "C1 to 6 alkyl group” in R 1 may be a straight chain or a branched chain.
  • C1 ⁇ 6 alkyl group” in R 1 include methyl group, ethyl group, n- propyl group, n- butyl group, n- pentyl group, n- hexyl, i- propyl, i- butyl, s -Butyl group, t-butyl group, i-pentyl group, neopentyl group, 2-methylbutyl group, i-hexyl group and the like can be mentioned.
  • the "C2-6 alkenyl group" in R 1 includes a vinyl group, a 1-propenyl group, a 2-propenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-methyl-2-propenyl group, and the like.
  • 2-Methyl-2-propenyl group 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-methyl-2-butenyl group, 2-methyl-2-butenyl group, 1-hexenyl Examples thereof include a group, a 2-hexenyl group, a 3-hexenyl group, a 4-hexenyl group, a 5-hexenyl group and the like.
  • the "C2-6 alkynyl group" in R 1 includes an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynyl group, a 1-methyl-2-propynyl group, and the like.
  • C1 ⁇ 6 alkyl group in R 1, the substituent on the "C2 ⁇ 6 alkenyl group", or “C2 ⁇ 6 alkynyl group” refers to fluoro, chloro, bromo group, a halogeno group such as iodo groups; hydroxyl C1-6 alkoxy groups such as methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group; 2,3-dichlorobutoxy C1-6 haloalkoxy groups such as groups, trifluoromethoxy groups, 2,2,2-trifluoroethoxy groups; methylthio groups, ethylthio groups, n-propylthio groups, i-propylthio groups, n-butylthio groups, i-butylthio groups C1-6 alkylthio groups such as groups, s-butylthi
  • Examples of the "C3 to 6 cycloalkyl group" in R 1 include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group and the like.
  • Examples of the "5- to 6-membered cyclic ether group" in R 1 include a tetrahydrofuranyl group and a tetrahydropyranyl group.
  • Substituent on "C3 ⁇ 8 cycloalkyl group" in R 1 is fluoro, chloro, bromo group, a halogeno group such as iodo groups; methyl, ethyl, n- propyl, i- propyl radical, n C1-6 alkyl groups such as -butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl group, n-hexyl group; difluoromethyl group, trifluoromethyl group, 1,2-dichloro C1-6 haloalkyl groups such as -n-propyl group, 1-fluoro-n-butyl group; hydroxyl groups; methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, C1-6 alkoxy groups such as i-butoxy group, t-butoxy group; C
  • R 1 is preferably a substituted or unsubstituted C1 to 6 alkyl group or a 5 to 6 member cyclic ether group.
  • Substituents on the "C1-6 alkyl group" in R 1 are a halogeno group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C1-6 alkylthio group, a C1-6 alkylsulfinyl group, a C1-6 alkylsulfonyl group. Groups or C3-6 cycloalkyl groups are preferred.
  • R 2 represents a substituted or unsubstituted C1 ⁇ 6 alkyl group, a substituted or unsubstituted C2 ⁇ 6 alkenyl group or a substituted or unsubstituted C2 ⁇ 6 alkynyl group,.
  • "Unsubstituted C1 ⁇ 6 alkyl group” in R 2 specific examples of the "substituted or unsubstituted C2 ⁇ 6 alkenyl group", or “substituted or unsubstituted C2 ⁇ 6 alkynyl group”, exemplified in R 1 You can list the same things that you did.
  • Substituent on "C1 ⁇ 6 alkyl group" in R 2 is fluoro, chloro, bromo group, a halogeno group such as iodo group; methoxy group, ethoxy group, n- propoxy group, i- propoxy, n- C1-6 alkoxy groups such as butoxy group, s-butoxy group, i-butoxy group, t-butoxy group; C1-6 alkoxy C1-6 alkoxy groups such as methoxyethoxy group; 2,3-dichlorobutoxy group, trifluoro C1-6 haloalkoxy groups such as methoxy group, 2,2,2-trifluoroethoxy group; methylthio group, ethylthio group, n-propylthio group, i-propylthio group, n-butylthio group, i-butylthio group, s- C1-6 alkylthio groups such as butylthio group, t-butyl
  • the nitrogen atom, 1 to 4 hetero atoms selected from the group consisting of an oxygen atom and a sulfur atom Is a group of a 5-membered aromatic ring containing as a constituent atom of the ring.
  • Examples of the 5-membered heteroaryl group include a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isooxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group and a tetrazolyl group. Can be done.
  • R 3 is a hydrogen atom, a substituted or unsubstituted C1 to 6 alkyl group, a substituted or unsubstituted C2 to 6 alkenyl group, a substituted or unsubstituted C2 to 6 alkynyl group, a substituted or unsubstituted C1 to 6 alkoxy group. , Substituted or unsubstituted C3-6 cycloalkyl group, or substituted or unsubstituted phenyl group. Specific examples of these groups in R 3 include the same as those illustrated in R 1.
  • the "C1 ⁇ 6 alkoxy group" in R 3 a methoxy group, an ethoxy group, n- propoxy group, n- butoxy group, n- pentyloxy group, n- hexyloxy group, i- propoxy, i- butoxy , S-butoxy group, t-butoxy group, i-hexyloxy group and the like.
  • Substituents on the "C1-6 alkoxy group" in R 3 are halogeno groups such as fluoro groups, chloro groups, bromo groups, iodo groups; hydroxyl groups; methoxy groups, ethoxy groups, n-propoxy groups, i-propoxy groups, C1-6 alkoxy groups such as n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group; 2,3-dichlorobutoxy group, trifluoromethoxy group, 2,2,2-trifluoroethoxy group C1-6 haloalkoxy groups such as methylthio group, ethylthio group, n-propylthio group, i-propylthio group, n-butylthio group, i-butylthio group, s-butylthio group, t-butylthio group and the like.
  • halogeno groups such as fluoro groups, chloro groups, bromo
  • C1-6 alkylsulfinyl group such as methylsulfinyl group, ethylsulfinyl group, t-butylsulfinyl group
  • C1-6alkylsulfonyl group such as methylsulfonyl group, ethylsulfonyl group, t-butylsulfonyl group
  • cyclopropyl group C3-6 cycloalkyl groups such as cyclobutyl group, cyclopentyl group, cyclohexyl group
  • phenyl group; C1 such as 4-methylphenyl group, 4-chlorophenyl group, 4-trifluoromethylphenyl group, 4-trifluoromethoxyphenyl group
  • Substituent on the "phenyl group" in R 3 is fluoro, chloro, bromo group, a halogeno group such as iodo groups; methyl, ethyl, n- propyl, i- propyl, n- butyl group, C1-6 alkyl groups such as s-butyl group, i-butyl group, t-butyl group, n-pentyl group, n-hexyl group; difluoromethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl Group, C1-6 haloalkyl group such as 1-fluoro-n-butyl group; hydroxyl group; methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group , C1-6 alkoxy groups such as t-butoxy group; C1-6 haloalkoxy groups such
  • R 3 is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, or a substituted or unsubstituted C2-6 alkynyl group. It is preferably a C3 to 6 cycloalkyl group of. "C1 ⁇ 6 alkyl group" in R 3, the substituent on "C2 ⁇ 6 alkenyl group", or “C2 ⁇ 6 alkynyl group", halogeno groups are preferable.
  • the substituent on the "C3 to 6 cycloalkyl group” is preferably a halogeno group or a C1 to 6 alkyl group.
  • [Q] Q indicates a substituted or unsubstituted phenyl group or a substituted or unsubstituted naphthyl group.
  • the substituent (sometimes referred to as substituent (X)) on the "phenyl group” or “naphthyl group” in Q is a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2.
  • R independently represents a substituted or unsubstituted C1 to 6 alkyl group or a substituted or unsubstituted C3 to 6 cycloalkyl group, respectively.
  • R a each independently represent a hydrogen atom, a substituted or unsubstituted C1 ⁇ 6 alkyl group or a substituted or unsubstituted C1 ⁇ 6 alkoxy group,.
  • R b represents a substituted or unsubstituted C1-6 alkyl group or a substituted or unsubstituted phenyl group.
  • R c represents a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group.
  • R 2 N-CO- the group represented by R 2 N-CO-NH-, the group represented by R 2 N-CO-CO-NH-, or the group represented by R 2 N.
  • R and R may be bonded to form a 4- to 6-membered ring together with the nitrogen atom to which they are bonded.
  • R and R may be bonded to form a 5- to 6-membered ring together with the sulfur atom to which they are bonded.
  • X is a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a hydroxyl group, a substituted or unsubstituted C1-6 alkoxy.
  • halogeno group examples include a fluoro group, a chloro group, a bromo group, an iod group and the like.
  • the "C1 to 6 alkyl group” in X may be a straight chain or a branched chain.
  • the "C1 to 6 alkyl groups” in X include methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, i-propyl group, i-butyl group and s-. Butyl group, t-butyl group, i-pentyl group, neopentyl group, 2-methylbutyl group, i-hexyl group and the like can be mentioned.
  • the "C2-6 alkenyl group" in X includes a vinyl group, a 1-propenyl group, a 2-propenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-methyl-2-propenyl group, and 2 -Methyl-2-propenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-methyl-2-butenyl group, 2-methyl-2-butenyl group, 1-hexenyl group , 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group and the like.
  • the "C2-6 alkynyl group" in X includes an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynyl group, a 1-methyl-2-propynyl group, and 2 -Methyl-3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 2-methyl-3-pentynyl group, 1-hexynyl group , 1,1-dimethyl-2-butynyl group and the like.
  • Examples of the "C1 to 6 alkoxy group" in X include a methoxy group, an ethoxy group, an n-propoxy group, an n-butoxy group, an n-pentyloxy group, an n-hexyloxy group, an i-propoxy group, and an i-butoxy group. Examples thereof include an s-butoxy group, a t-butoxy group, and an i-hexyloxy group.
  • Examples of the "C2 to 6 alkenyloxy group" in X include a vinyloxy group, an allyloxy group, a propenyloxy group, a butenyloxy group and the like.
  • Examples of the "C2 to 6 alkynyloxy group" in X include an ethynyloxy group and a propargyloxy group.
  • Examples of the "C1 to 6 alkylthio group" in X include a methylthio group, an ethylthio group, an n-propylthio group, an n-butylthio group, an n-pentylthio group, an n-hexylthio group, and an i-propylthio group.
  • Examples of the "C1 to 6 alkylsulfinyl group" in X include a methylsulfinyl group, an ethylsulfinyl group, and a t-butylsulfinyl group.
  • Examples of the "C1 to 6 alkylsulfonyl group" in X include a methylsulfonyl group, an ethylsulfonyl group, and a t-butylsulfonyl group.
  • Substituents on the "C1-6 alkyl group” or “C1-6 alkoxy group” in X are halogeno groups such as fluoro group, chloro group, bromo group, iodo group; hydroxyl group; methoxy group, ethoxy group, n-propoxy.
  • C1-6 alkoxy groups such as groups, i-propoxy groups, n-butoxy groups, s-butoxy groups, i-butoxy groups, t-butoxy groups; C1-6 alkoxy C1-6 alkoxy groups such as methoxyethoxy groups; cyclo C3-6 cycloalkyl C1-6 alkoxy groups such as propylmethoxy group; 2,3-dichlorobutoxy group, trifluoromethoxy group, 2,2,2-trifluoroethoxy group, 3,3,3-trifluoropropoxy group C1-6 haloalkoxy groups such as methylthio group, ethylthio group, n-propylthio group, i-propylthio group, n-butylthio group, i-butylthio group, s-butylthio group, t-butylthio group and the like C1-6 alkylthio Group; C1-6 alkylsulfinyl group such as methylsulfinyl
  • C2-6 alkenyl group such as fluoro groups, chloro groups, bromo groups and iodo groups; hydroxyl groups; methoxy groups, ethoxy groups, n-propoxy groups, i-propoxy groups, n-butoxy groups, s- C1-6 alkoxy groups such as butoxy group, i-butoxy group, t-butoxy group; C1-6 haloalkoxy groups such as 2,3-dichlorobutoxy group, trifluoromethoxy group, 2,2,2-trifluoroethoxy group Group; C1-6 alkylsulfonyl group such as methylsulfonyl group, ethylsulf
  • Examples of the "C3 to 6 cycloalkyl group” in X include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group and the like.
  • Examples of the "C3 to 6 cycloalkyloxy group” in X include a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group, a cyclohexyloxy group, and a cycloheptyloxy group.
  • the "5- to 6-membered heterocyclyl group" in X is a 5-membered ring or 6-membered ring containing 1, 2, 3 or 4 heteroatoms selected from the group consisting of nitrogen atom, oxygen atom and sulfur atom as ring constituent atoms. It is the base of the ring. When there are two or more heteroatoms, they may be the same or different.
  • Examples of the "5- to 6-membered heterocyclyl group” include a 5- to 6-membered saturated heterocyclyl group, a 5- to 6-membered unsaturated heterocyclyl group, and a 5- to 6-membered heteroaryl group.
  • Examples of the 5- to 6-membered saturated heterocyclyl group include a pyrrolidinyl group, a tetrahydrofuranyl group, a dioxolanyl group, a tetrahydropyranyl group, a piperidyl group, a piperazinyl group, a morpholinyl group, and a dioxanyl group.
  • the 5- to 6-membered unsaturated heterocyclyl group includes a pyrrolinyl group, a dihydrofuranyl group, an imidazolinyl group, a pyrazolinyl group, an oxazolinyl group, an isooxazolinyl group, a thiazolinyl group, an isothiazolinyl group, a dihydropyranyl group and a dihydrooxadinyl group. And so on.
  • Examples of the 5-membered heteroaryl group include a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isooxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group and a tetrazolyl group. Can be done.
  • 6-membered heteroaryl group examples include a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridadinyl group, a triazinyl group and the like.
  • the "5- to 6-membered heterocyclyloxy group" in X has a structure in which a 5- to 6-membered heterocyclyl group and an oxy group are bonded. Specific examples include a thiazolyloxy group and a pyridyloxy group.
  • the substituent on the "phenylsulfonyl group” is a halogeno group such as a fluoro group, a chloro group, a bromo group, an iodo group; a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, s.
  • C1-6 alkyl groups such as -butyl group, i-butyl group, t-butyl group, n-pentyl group, n-hexyl group; difluoromethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group , C1-6 haloalkyl groups such as 1-fluoro-n-butyl group; hydroxyl groups; methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, C1-6 alkoxy group such as t-butoxy group; C1-6 haloalkoxy group such as 2,3-dichlorobutoxy group, trifluoromethoxy group, 2,2,2-trifluoroethoxy group; oxo group; or cyano group ; Is preferable.
  • R, R a , R b , or R c include the same as illustrated in X.
  • R-CO- examples include an acetyl group and a cyclopropylcarbonyl group.
  • examples of the "group represented by RO-CO-" in X include a methoxycarbonyl group and the like.
  • Examples of the " group represented by R-CONR a- " in X include an acetamide group and a cyclopropanecarboxyamide group. Examples of the "group represented by RNH-CO-" in X include a methylaminocarbonyl group and the like.
  • Examples of the "group represented by R 2 N-CO-" in X include a dimethylaminocarbonyl group and the like.
  • R and R may be bonded to form a 4- to 6-membered ring together with the nitrogen atom to which they are bonded, and the 4- to 6-membered ring to be formed includes an azetidine ring, a pyrrolidine ring, a piperidine group, and a piperazine. Rings, morpholine rings, etc. can be mentioned.
  • Examples of the "group represented by R 2 N-CO-" after forming a 4- to 6-membered ring include an azetidine-1-carbonyl group, a pyrrolidine-1-carbonyl group, and a morpholin-4-carbonyl group. it can.
  • Examples of the "group represented by RO-CO-NR a- " in X include a (t-butoxycarbonyl) amino group and a methoxy (t-butoxycarbonyl) amino group.
  • Examples of the "group represented by RNH-CO-NH-" in X include methylaminocarboxyamide.
  • Examples of the " group represented by R 2 N-CO-NH-" in X include dimethylaminocarboxyamide and the like.
  • R and R may be bonded to form a 4- to 6-membered ring together with the nitrogen atom to which they are bonded, and specific examples of the 4- to 6-membered ring to be formed include the above-mentioned "R 2 N-”.
  • the same ones as exemplified in "Group represented by CO-" can be mentioned.
  • Examples of the "group represented by R 2 N-CO-NH-" after forming a 4- to 6-membered ring include an azetidine-1-carboxyamide group, a pyrrolidine-1-carboxyamide group, and a morpholine-4-carboxyamide. Can be mentioned.
  • Examples of the "group represented by RNH-CO-CO-NH-" in X include methylaminocarbonylcarboxyamide and the like.
  • Examples of the "group represented by R 2 N-CO-CO-NH-” in X include dimethylaminocarbonylcarboxyamide and the like.
  • R and R may be bonded to form a 4- to 6-membered ring together with the nitrogen atom to which they are bonded, and specific examples of the 4- to 6-membered ring to be formed include the above-mentioned "R 2 N-”.
  • the same ones as exemplified in "Group represented by CO-" can be mentioned.
  • the "group represented by R 2 N-CO-NH-" after forming the 4- to 6-membered ring includes azetidine-1-carbonylcarboxyamide group, pyrrolidine-1-carbonylcarboxyamide group, and morpholin-4-carbonyl. Carboxamide and the like can be mentioned.
  • Examples of the " group represented by RS (O) 2- NH-" in X include methyl sulfonamide.
  • X - it includes "R 2 N-S (O) 2 group represented by” may be mentioned, methyl sulfonamide.
  • R and R may be bonded to form a 4- to 6-membered ring together with the nitrogen atom to which they are bonded, and specific examples of the 4- to 6-membered ring to be formed include the above-mentioned "R 2 N-”.
  • the same ones as exemplified in "Group represented by CO-" can be mentioned.
  • R and R may be bonded to form a 5- to 6-membered ring together with the sulfur atom to which they are bonded, and the 5 to 6-membered ring to be formed includes a tetrahydrothiophene ring and a tetrahydro-2H-thiopyran ring.
  • a "divalent organic group that can be formed by two Xs together" is a substituted or unsubstituted saturated divalent hydrocarbon group having 1 to 4 carbon atoms; or from O, N, and S.
  • the divalent organic group that can be formed by two Xs together is a substituted or unsubstituted unsaturated hydrocarbon group having 2 to 3 carbon atoms; or O, N, and S.
  • a divalent group consisting of a group containing one or more heteroatoms selected from the group consisting of two or more heteroatoms and a divalent hydrocarbon group having 2 to 3 substituted or unsubstituted unsaturated carbon atoms. Is the basis of.
  • saturated divalent hydrocarbon group having 1 to 4 carbon atoms examples include "C1 to 4alkylene groups” such as a methylene group, a dimethylene group, a trimethylene group and a tetramethylene group.
  • C2 to 3 alkenylene groups can be mentioned.
  • the substituent on the "saturated or unsaturated divalent hydrocarbon group” is preferably a halogen group, a C1 to 6 alkyl group, or a C1 to 6 haloalkyl group.
  • Examples of the group containing an oxygen atom (O) include an oxy (-O-) group, a carbonyl (-C (O)-) group, a carboxy (-COO-) group and the like.
  • Examples of the divalent group formed by bonding an oxygen atom (O) -containing group and a saturated divalent hydrocarbon group include "oxy C2 to 3" such as an oxydimethylene group (-O-CH 2 CH 2-).
  • Alkylene group such as dimethyleneoxy group (-CH 2 CH 2 -O-), "oxy C1-2” such as oxymethyleneoxy group (-O-CH 2-O-) Alkyleneoxy group ”, methyleneoxymethylene group (-CH 2- O-CH 2- ), methyleneoxydimethylene group (-CH 2- O-CH 2 CH 2- ), dimethyleneoxymethylene group (-CH 2 CH)
  • alkyleneoxy C1-2 alkylene groups such as 2- O-CH 2-).
  • Examples of the group containing a nitrogen atom (N) include an imino (-NH-) group, an N-substituted imino group, an iminooxy (-NH- ⁇ -) group, an N-substituted iminooxy group, and an oxyimino (- ⁇ -NH-).
  • Examples of the divalent group formed by bonding a group containing a nitrogen atom (N) and a saturated divalent hydrocarbon group include "imino C2 to 3" such as an iminodimethylene group (-NH-CH 2 CH 2-).
  • Alkylene group such as dimethylene imino group (-CH 2 CH 2- NH-), "imino C1-2 such as imimethylene imino group (-NH-CH 2-NH-)" Alkylene imino group ”, methylene imino methylene group (-CH 2- NH-CH 2- ), methylene imino dimethylene group (-CH 2- NH-CH 2 CH 2- ), dimethylene imino methylene group (-CH 2 CH)
  • Examples thereof include "C1-2 alkylene imino C1-2 alkylene groups” such as 2- NH-CH 2-).
  • Examples of the group containing a sulfur atom (S) include a thio (-S-) group, a sulfinyl (-S (O)-) group, and a sulfonyl (-S (O) 2- ) group.
  • the divalent group formed by bonding a group containing a sulfur atom (S) and a saturated divalent hydrocarbon group includes a thiodimethylene group (-S-CH 2 CH 2- ) and a thiotrimethylene group (-S-).
  • the "divalent organic group that can be formed by two Xs together" is a substituted or unsubstituted saturated divalent hydrocarbon group having 1 to 4 carbon atoms; or O and A divalent group consisting of a group containing one or more heteroatoms selected from the group consisting of S and a divalent hydrocarbon group having 1 to 4 substituted or unsubstituted saturated carbon atoms. It is preferable that it is a group of.
  • the group containing an oxygen atom (O) is preferably an oxy (-O-) group, and the group containing a sulfur atom (S) is a thio (-S-) group or a sulfonyl (-S (O) 2). -) Groups are preferred.
  • Q is preferably a substituted or unsubstituted phenyl group.
  • the compound (I) when Q is a substituted or unsubstituted phenyl group is shown in the formula (I-1).
  • R 1 to R 3 have the same meanings as those in formula (I).
  • X indicates the substituent on the phenyl group mentioned above.
  • n represents an integer from 0 to 5. When n is 2 or more, X may be the same or different. When n is 2 or more, two Xs thereof may be combined to form a divalent organic group.
  • the compound represented by the above formula (I-1) is preferably a compound represented by the following formula (I-3).
  • R 1 ⁇ R 3 have the same meanings as those in formula (I).
  • X 1 is a halogeno group, a substituted or unsubstituted C1 to 6 alkyl group, a substituted or unsubstituted C2 to 6 alkenyl group, a substituted or unsubstituted C2 to 6 alkynyl group, a substituted or unsubstituted C1 to 6 alkoxy group.
  • Substituent or unsubstituted C1-6 alkylthio group substituted or unsubstituted C1-6 alkylsulfinyl group, substituted or unsubstituted C1-6 alkylsulfonyl group, substituted or unsubstituted C3-6 cycloalkyl group, substituted or It represents an unsubstituted phenyl group, a substituted or unsubstituted 5- to 6-membered heterocyclyl group, a nitro group, or a cyano group.
  • m represents an integer of 0 to 3. When m is 2 or more, X 1 may be the same or different. Specific examples of these groups in X 1 include the same as illustrated in X.
  • C1 ⁇ 6 alkyl group in X 1, "C2 ⁇ 6 alkenyl group”, “C2 ⁇ 6 alkynyl group”, “C1 ⁇ 6 alkoxy group”, “C1 ⁇ 6 alkylthio group”, “C1 ⁇ 6 alkylsulfinyl group ,
  • the substituent on the "C1-6 alkylsulfonyl group” is preferably a halogeno group.
  • the substituent on the "C3 to 6 cycloalkyl group” is preferably a halogeno group or a C1 to 6 alkyl group.
  • Substituents on the "phenyl group” or "5-6-membered heterocyclyl group” are halogeno groups, C1-6 alkyl groups, C1-6 haloalkyl groups, C1-6 alkoxy groups, C1-6 haloalkoxy groups, or cyano groups. Is preferable.
  • salt of compound (I) examples include alkali metal salts such as lithium, sodium and potassium; alkaline earth metal salts such as calcium and magnesium; transition metal salts such as iron and copper; ammonium salts; triethylamine and tributylamine. , Salts of organic bases such as pyridine, hydrazine; and the like.
  • the structure of compound (I) or the salt of compound (I) can be determined by an NMR spectrum, an IR spectrum, an MS spectrum, or the like.
  • Compound (I) is not particularly limited depending on the production method thereof. Further, the salt of compound (I) can be obtained from compound (I) by a known method. Compound (I) can be produced, for example, by using the compound obtained by the production method described in Patent Document 1 as a production intermediate thereof, and by the method described in Examples and the like.
  • reaction scheme 1 For example, compound (I) can be prepared from compound of formula (2) as shown in Reaction Scheme 1 below.
  • the symbols in formula (2) have the same meaning as those in formula (I).
  • the compound of formula (2) is reacted with a halogenating agent to construct an ⁇ -haloketone structure in the molecule, and the compound of formula (2Xa) is prepared, followed by R 2 ONa. It can be prepared by reacting with an alkoxide such as (if R 2 is a methyl group, sodium methoxide is applicable).
  • Xa in the formula (2Xa) represents a halogeno group such as a chloro group or a bromo group.
  • the compound of formula (2Xa) may be unstable and it is preferable to carry out the subsequent reaction without isolation.
  • reaction scheme 2 The compound of formula (2) can be prepared from the compound of formula (3) as shown in Reaction Scheme 2 below.
  • the symbols in formula (3) have the same meaning as those in formula (I).
  • R x represents a lower alkyl group, such as a methyl group.
  • R x has the same meaning.
  • the compound of formula (2) can be prepared by heating the compound of formula (3) with morpholine.
  • reaction scheme 3 The compound of formula (3) can be prepared by condensing the compound of formula (4) with the compound of formula (5) as shown in the following reaction scheme 3.
  • the symbols in formula (4) have the same meaning as those in formula (I).
  • R y represents a lower alkyl group such as a methyl group or an ethyl group. Further, R y may be bonded to each other to form a 1,3,2-dioxaborolane ring.
  • Q in the formula (5) has the same meaning as Q in the formula (I).
  • X b represents a halogeno group.
  • the compounds of formula (3) are suitable bases (eg, inorganic bases such as potassium phosphate or cesium fluoride), metal catalysts (eg, palladium catalysts such as Pd (OAc) 2 ) and optionally ligands (eg, phosphine). It can be prepared by reacting the compound of the formula (4) with the compound of the formula (5) in the presence of a ligand). Metal catalysts and ligands are added as preformed complexes (eg, palladium / phosphine complexes such as bis (triphenylphosphine) palladium dichloride or [1,1-bis (diphenylphosphino) ferrocene] palladium dichloride dichloromethane adduct).
  • bases eg, inorganic bases such as potassium phosphate or cesium fluoride
  • metal catalysts eg, palladium catalysts such as Pd (OAc) 2
  • ligands eg, phosphine
  • Q in the compound of the formula (5) indicates a substituted or unsubstituted phenyl group or a substituted or unsubstituted naphthyl group, but the phenyl group and the substituent on the naphthyl group may be appropriately converted after the reaction. ..
  • reaction scheme 4 The compound of formula (4) can be prepared from the compound of formula (6) as shown in Reaction Scheme 4 below.
  • the symbols in formula (6) have the same meaning as those in formula (I).
  • the compound of formula (4) is a suitable base (eg, an inorganic base such as potassium phosphate or cesium fluoride), a metal catalyst (eg, a palladium catalyst such as Pd 2 (dba) 3 , (Pd (OAc) 2 )).
  • a metal catalyst eg, a palladium catalyst such as Pd 2 (dba) 3 , (Pd (OAc) 2
  • a ligand eg, a phosphine ligand
  • it can be prepared by reacting the compound of formula (6) with a boronic acid or ester of boronic acid, eg, bis (pinacolato) diboron.
  • Metal catalysts and ligands are added as preformed complexes (eg, palladium / phosphine complexes such as bis (triphenylphosphine) palladium dichloride or [1,1-bis (diphenylphosphino) ferrocene] palladium dichloride dichloromethane adduct).
  • palladium / phosphine complexes such as bis (triphenylphosphine) palladium dichloride or [1,1-bis (diphenylphosphino) ferrocene] palladium dichloride dichloromethane adduct.
  • palladium / phosphine complexes such as bis (triphenylphosphine) palladium dichloride or [1,1-bis (diphenylphosphino) ferrocene] palladium dichloride dichloromethane adduct.
  • reaction scheme 5 The compound of formula (6) can be prepared from the compound of formula (7) as shown in Reaction Scheme 5 below.
  • the symbols in formula (7) have the same meaning as those in formula (I).
  • the compound of formula (6) can be prepared by reacting the compound of formula (7) with a suitable metal alkoxide, for example sodium methoxide.
  • a suitable metal alkoxide for example sodium methoxide.
  • the compound of formula (7) can be prepared by a known method.
  • reaction scheme 3A The compound of formula (3) can be prepared by condensing the compound of formula (6) with the compound of formula (8) as shown in the following reaction scheme 3A.
  • Q in the formula (8) has the same meaning as Q in the formula (I).
  • R y represents a lower alkyl group such as a methyl group or an ethyl group. Further, R y may be bonded to each other to form a 1,3,2-dioxaborolane ring.
  • the compounds of formula (3) are suitable bases (eg, inorganic bases such as potassium phosphate or cesium fluoride), metal catalysts (eg, palladium catalysts such as Pd (OAc) 2 ) and optionally ligands (eg, phosphine). It can be prepared by reacting the compound of formula (6) with the compound of formula (8) in the presence of a ligand). Metal catalysts and ligands are added as preformed complexes (eg, palladium / phosphine complexes such as bis (triphenylphosphine) palladium dichloride or [1,1-bis (diphenylphosphino) ferrocene] palladium dichloride dichloromethane adduct). Can be.
  • inorganic bases such as potassium phosphate or cesium fluoride
  • metal catalysts eg, palladium catalysts such as Pd (OAc) 2
  • ligands eg, phosphine
  • Q in the compound of the formula (8) indicates a substituted or unsubstituted phenyl group or a substituted or unsubstituted naphthyl group, but the phenyl group and the substituent on the naphthyl group may be appropriately converted after the reaction. ..
  • the compound of the present invention exhibits high herbicidal activity in both soil treatment and foliage treatment under upland farming conditions.
  • the compound of the present invention is effective for various field weeds and may show selectivity for crops such as corn and wheat.
  • the compound of the present invention may exhibit a plant growth regulating effect such as a growth inhibitory effect on useful plants such as crops, ornamental plants, and fruit trees.
  • the compound of the present invention has an excellent herbicidal effect on paddy weeds and may show selectivity for rice.
  • the herbicide of the present invention contains at least one selected from the group consisting of compound (I) and a salt of compound (I) as an active ingredient. That is, one aspect of the present invention is a herbicide containing at least one selected from the group consisting of compound (I) and a salt thereof as an active ingredient.
  • the herbicide of the present invention exhibits high herbicidal activity in both soil treatment and foliage treatment under upland farming conditions.
  • the herbicide of the present invention has an excellent herbicidal effect on paddy weeds such as Nobie, Cyperus difformis, Sagittaria trifolia, and Scirpus juncoides, and may show selectivity for rice. Further, the herbicide of the present invention can also be applied to control weeds in orchards, lawns, railroad tracks, vacant lots and the like.
  • Useful plants for which the herbicides of the invention can be used include crops such as cereals and wheat, cotton, oilseed rape, sunflower, corn, rice, soybeans, sugar beet, sugar cane and lawn. Crops can also include trees such as fruit trees, palm trees, coconut trees or other nuts. It also includes vines such as vines, fruit shrubs, fruit plants and vegetables.
  • the field weeds to be controlled include the following weeds.
  • A Monocolobed weeds (1) Weeds of the family Cyperaceae Weeds of the genus Cyperus, such as Cyperus esculentus, Cyperus iria, Cyperus iria, Cyperus microiria rotundus).
  • Alopecurus weeds such as Alopecurus aequalis and Blackgrass (Alopecurus myosuroides); Weeds of the genus Silkybent (Apera), such as Silkybent (Apera spica-venti); Weeds of the genus Oat (Avena), such as Enbaku (Avena sativa); Bromes weeds, such as Bromes japonicus, Bromes sterilis; Weeds of the genus Digitaria (Digitaria), such as Digitaria ciliaris, Digitaria sanguinalis; Weeds of the genus Echinochloa, such as Echinochloa crus-galli; Weeds of the genus Goosegrass (Eleusine), such as Goosegrass (Eleusine indica); Ryegrass (Lolium) weeds, such as Italian ryegrass (Lolium multiflorum Lam.); Panicgrass
  • (B) Twin leaf weeds (1) Amaranthaceae weeds Amaranthus blitum weeds, such as Amaranthus blitum, Amaranthus palmeri, Amaranthus retroflexus, Amaranthus rudis; Weeds of the genus Goosefoot (Chenopodium), such as white goosefoot (Chenopodium album); Weeds of the genus Bassia, such as Bassia scoparia.
  • Asteraceae weeds Weeds of the genus Ragweed (Ambrosia), such as ragweed (Ambrosia artemisiifolia) and giant ragweed (Ambrosia trifida); Weeds of the genus Conyza, such as horseweed (Conyza canadensis) and erigeron sumatren (Conyza sumatrensis); Weeds of the genus Fleabane (Erigeron), such as Erigeron annuus; Weeds of the genus Mayweed (Matricaria), such as Tripleurospermum (Matricaria inodora), Chamomile (Matricaria recutita); Weeds of the genus Xanthium, such as the cocklebur (Xanthium occidentale).
  • Ambrosia ragweed
  • Weeds of the genus Conyza such as horseweed (Con
  • paddy weeds to be controlled include the following weeds.
  • A Monocotyledonous weeds
  • Echinochloa weeds (so-called nobies) weeds, such as Echinochloa oryzoides, Echinochloa crus-galli; Leersia weeds, such as Leersia japonica; Weeds of the genus Paspalum, such as Paspalum distichum.
  • Weeds of the family Pontederiaceae Weeds of the genus Monochoria, such as Monochoria korsakowii, Pontederia vaginalis (Monochoria vaginalis var. Plantaginea).
  • the herbicide of the present invention may consist only of the compound of the present invention, or may be in a dosage form generally available as a pesticide, for example, a wettable powder, a granule, a powder, an emulsion, a water solvent, a suspension, or a flowable. It may be a formulation such as.
  • one aspect of the invention is a herbicide comprising an agrochemically acceptable solid carrier and / or a liquid carrier.
  • a herbicide comprising an agrochemically acceptable solid carrier and / or a liquid carrier.
  • solid dosage forms vegetable powders such as soybean flour and wheat flour, diatomaceous earth, ashstone, talc, talc, bentonite, pyrophyllite, clay and other mineral fine powders, sodium benzoate, urea, and sardine.
  • Solid carriers such as organic and inorganic compounds such as, etc. can be used.
  • liquid dosage forms petroleum fractions such as kerosene, xylene and solventnaphtha, cyclohexane, cyclohexanone, dimethylformamide, dimethyl sulfoxide, alcohol, acetone, trichloroethylene, methyl isobutyl ketone, mineral oil, vegetable oil, water Liquid carriers such as can be used.
  • a surfactant can be added as needed.
  • Surfactants include alkylphenyl ethers with polyoxyethylene added, alkyl ethers with polyoxyethylene added, higher fatty acid esters with polyoxyethylene added, sorbitan higher fatty acid esters with polyoxyethylene added, and polyoxyethylene.
  • Nonionic surfactant such as added tristyrylphenyl ether, sulfate ester salt of alkylphenyl ether added with polyoxyethylene, alkylnaphthalene sulfonate, polycarboxylate, lignin sulfonate, alkylnaphthalene sulfonate
  • examples of the formaldehyde condensate, isobutylene-maleic anhydride copolymer and the like can be mentioned.
  • the concentration of the active ingredient can be appropriately set according to the dosage form.
  • the concentration of the active ingredient in the wettable powder is preferably 5 to 90% by weight, more preferably 10 to 85% by weight.
  • the concentration of the active ingredient in the emulsion is preferably 3 to 70% by weight, more preferably 5 to 60% by weight.
  • the concentration of the active ingredient in the granules is preferably 0.01 to 50% by weight, more preferably 0.05 to 40% by weight.
  • the wettable powder or emulsion thus obtained is diluted with water to a predetermined concentration to form a suspension or emulsion, and the granules are directly sprayed or mixed on the soil before or after germination of weeds. be able to.
  • an appropriate amount of 0.1 g or more of the active ingredient can be applied per hectare.
  • the herbicide of the present invention includes known fungicides, fungicides, insecticides, insecticides, acaricides, acaricides, herbicides, herbicides, plant growth regulators, fertilizers, and chemical damage reduction. It can also be mixed with an agent (safener) or the like. In particular, it is possible to reduce the amount of drug used by using it in combination with a herbicide. In addition to saving labor, a higher effect can be expected due to the synergistic action of the mixed drug. In that case, a combination with a plurality of known herbicides is also possible. That is, one aspect of the present invention is a herbicide containing one or more additional herbicidal active ingredients. In addition, one of the aspects of the present invention is a herbicide containing one or more additional phytotoxicity reducing agents.
  • herbicidal active ingredients used in the present invention are not particularly limited, and examples thereof include the following.
  • Pyridadinone type is carbamate type such as desmedipham, phenmedipham, swep; chlorobromuron, chlorotoluron, chloroxuron, dimefuron, DCMU ( Diuron), ethidimuron, fenuron, fluometuron, isoproturon, isouron, linuron, metabenzthiazuron, metobromron Ureas such as metoxuron, monolinuron, neburon, siduron, tebuthiuron, metobenzuron, carbutilate; DCPA (propanil), CMMP (penta) Nocroll Amide system such as (pentanochlor); anilide system such as cypromid; nitrile system such as bromofenoxim, bromoxynil, ioxynil; benzothia dinone system such as bentazone.
  • Pyridazines such as pyridate and pyridaf
  • Bipyridylium-based substances such as diquat and paraquat; other substances that themselves become free radicals in the plant body and generate active oxygen to exhibit a fast-acting herbicidal effect.
  • oxazolidinedione system benzfendizone, butafenacil and other pyrimidinedione system; saflufenacil and other sulfonylamide system; flufenpyr-ethyl and other pyridazine system; Inhibiting chlorophyll biosynthesis in plants such as pyrachlonil, profluazol, tiafenacil, and trifludimoxazin, and abnormal accumulation of photosensitizing peroxides in the plant body. It is said to show herbicidal effect.
  • Glyphosates such as glyphosate, glyphosate-ammonium, glyphosate-isopropylamine, glyphosate trimesium (sulfosate); other EPSP synthase inhibitors
  • glufosinate h) Glyphosinate
  • glufosinate-ammonium phosphinic acid
  • phosphinic acid such as bialaphos (bilanafos), etc.
  • Glutamine synthase inhibition and other plant amino acid biosynthesis are said to show herbicidal effect. ..
  • Oxyacetamides such as flufenacet and mefenacet; fentrazami Tetrazolinones such as fentrazamide; other anilofos, indanofan, cafenstrole, piperophos, methiozolin, fenoxasulfone, pyroxasulfone, ip
  • the herbicidal effect is shown by inhibiting microtubule polymerization, microtubule formation, and cell division of plants such as fenoxasulfone, or by inhibiting very long chain fatty acid (VLCFA) biosynthesis. What has been done.
  • Nitrile type such as DBN (dichlobenil), DCBN (chlorthiamid); benzamide type such as isoxaben; triazolocarboxamide type such as flupoxam; quinclorac etc.
  • Quinoline carboxylic acid system Others It is said to show herbicidal effect by inhibiting cell wall (cellulose) synthesis such as triaziflam and indaziflam.
  • Thiocarbamates such as prosulfocarb, benthiocarb (thiobencarb), tiocarbazil, triallate, vernolate, diallate
  • phosphorodithio such
  • Phenoxycarboxylic acids such as clomeprop, 2,4-PA (2,4-D), 2,4-DB, dichlorprop, MCPA, MCPB, MCPP (mecoprop) System: Benzoic acid system such as chloramben, MDBA (dicamba), TCBA (2,3,6-TBA); clopyralid, aminopyralid, fluroxypyr, picloram , Triclopyr, halauxifen and other pyridinecarboxylic acid systems; quinclorac, quinmerac and other quinoline carboxylic acid systems; NPA (naptalam), diflufenzopyr ( Phthalamate semicarbazones such as diflufenzopyr; others Benazolin, diflufenzopyr, fluroxypyr, chlorflurenol, aminocyclopyrachlor, DAS534, etc. It is said to show herbicidal effect by disturbing the hormonal action of plants.
  • Benzoic acid system such as chloramben, MDBA (dicamba),
  • Arylaminopropionic acid type such as flamprop-isopropyl; pyrazolium type such as difenzoquat; organic arsenic type such as DSMA and MSMA; other bromobutide, (chlor)- Flurenol, cinmethylin, cumyluron, dazomet, daimuron, methyl-dymron, etobenzanid, hosamine, oxaziclomefone, oxaziclomefone (Oleic acid), pelargonic acid, pyributicarb, endothall, sodiumchlorate, metam, quinoclamine, cyclopyrimorate, tridiphan (Tridiphane), clacyfos and other herbicides.
  • Arylaminopropionic acid type such as flamprop-isopropyl
  • pyrazolium type such as difenzoquat
  • organic arsenic type such as DSMA
  • Examples of the phytotoxicity reducing agent (safener) that can be used in the present invention include benoxacor, cloquintocet, cloquintocet-mexyl, cyometrinil, and cyprosulfamide.
  • Cyprosulfamide dichlormid, dicyclonon, dietholate, fenchlorazole, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim , Furilazole, isoxadifen, isoxadifen-ethyl, mefenpyr, mefenpyr-diethyl, mephenate, naphthalic anhydride. ), Oxabetrinil and the like.
  • formulation example Although some examples of formulations relating to the herbicide of the present invention are shown, the compounds (active ingredients), additives and addition ratios of the present invention are not limited to the present examples and can be changed in a wide range.
  • the part in the formulation example indicates the part by weight.
  • Wettable powder 20 parts of the compound of the present invention 20 parts of white carbon 20 parts of diatomaceous earth 52 parts of sodium alkyl sulfate 8 parts or more are uniformly mixed and finely pulverized to obtain a wettable powder having 20% of the active ingredient.
  • Step 2 Synthesis of 3- (6-bromo-2-fluoro-3- (trifluoromethyl) phenyl) propanol-1-ol
  • the obtained organic layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The obtained crystals were dried to obtain 1.6 g of the target product.
  • Table 1 shows an example of the compound of the present invention produced by the same method as in the above synthesis example.
  • Table 1 shows the substituents in the compound represented by the formula (I-2).
  • the melting point is also shown as a physical characteristic value.
  • Me represents a methyl group
  • Et represents an ethyl group
  • n Pr represents an n-propyl group
  • i Pr represents an i-propyl group
  • c Pr represents a cyclopropyl group
  • t Bu represents a t-butyl group.
  • N Hex represents an n-hexyl group
  • Ph represents a phenyl group.
  • Table 2 shows an example of the compound of the present invention produced by the same method.
  • Table 3 shows an example of the compound of the present invention produced by the same method.
  • Table 3 shows the substituents in the compound represented by the formula (I-4).
  • Compound A-26 1 H-NMR (400MHz, CDCl 3 ): ⁇ 3.14 (s, 3H), 3.53 (s, 3H), 3.79 (s, 3H), 7.42-7.53 (m, 4H), 7.63- 7.65 (m, 2H), 7.89 (d, 1H), 7.95 (dd, 1H), 8.22 (d, 1H).
  • Compound A-28 1 H-NMR (400MHz, CDCl 3 ): ⁇ 3.10 (s, 3H), 3.49 (s, 3H), 3.51 (s, 3H), 3.74 (s, 3H), 4.56 (s, 2H), 7.20 (s, 1H), 7.71 (dd, 1H), 7.81 (d, 1H), 7.98 (d, 1H).
  • Compound A-31 1 H-NMR (400MHz, CDCl 3 ): ⁇ 3.50 (s, 3H), 3.68-3.77 (m, 10H), 4.01-4.14 (m, 4H), 7.20 (s, 1H), 7.61-7.63 (m, 2H), 8.97 (s, 1H).
  • Compound A-32 1 H-NMR (400MHz, CDCl 3 ): ⁇ 2.10 (s, 3H), 3.42-3.50 (m, 7H), 3.66-3.74 (m, 7H), 6.28 (s, 1H), 7.23 (s, 3H), 7.52-7.58 (m, 2H).
  • Compound A-41 1 H-NMR (400MHz, CDCl 3 ): ⁇ 2.05 (br, 3H), 2.11 (s, 3H), 2.28 (s, 3H), 3.51 (s, 3H), 3.68 (s, 3H), 3.96 (s, 3H), 7.13 (br, 1H), 7.19 (s, 1H), 7.39 (br, 1H).
  • Compound A-42 1 H-NMR (400MHz, CDCl 3 ): ⁇ 3.34 (s, 3H), 3.49 (s, 3H), 3.74 (s, 3H), 7.21 (s, 1H), 7.90 (d, 1H), 8.05 (d, 1H).
  • Compound A-43 1 H-NMR (400MHz, CDCl 3 ): ⁇ 2.55-2.68 (m, 6H), 3.15 (s, 3H), 3.65-3.67 (m, 6H), 7.28 (s, 1H), 7.60 (d, 1H), 7.96 (d, 1H).
  • Compound A-45 1 H-NMR (400MHz, CDCl 3 ): ⁇ 1.78 (s, 3H), 1.80 (s, 3H), 3.33 (s, 3H), 3.51 (s, 3H), 3.66 (s, 3H), 5.62 (d, 1H), 5.72 (d, 1H), 7.25 (s, 1H), 7.73 (d, 1H), 8.15 (d, 1H).
  • Compound A-52 1 H-NMR (400MHz, CDCl 3 ): ⁇ 3.54 (s, 3H), 3.71 (s, 3H), 7.31 (s, 1H), 7.68-7.75 (m, 2H), 7.85- 7.89 (m, 1H), 8.14 (s, 1H), 8.61 (s, 1H).
  • Compound A-53 1 H-NMR (400 MHz, CDCl 3 ): ⁇ 3.30 (s, 3H), 3.43 (s, 3H), 3.80 (s, 3H), 7.36 (dd, 1H), 7.49 (s) , 1H), 7.54-7.60 (m, 1H), 7.91 (dd, 1H).
  • Compound A-54 1 H-NMR (400 MHz, CDCl 3 ): ⁇ 0.70 (t, 3H), 1.45-1.54 (m, 2H), 3.10 (s, 3H), 3.38 (s, 3H), 3.77 (s, 3H), 3.93 (t, 2H), 7.90-7.97 (m, 2H), 8.21 (s, 1H).
  • Compound A-56 1 H-NMR (400MHz, CDCl 3 ): ⁇ 3.54 (s, 3H), 3.69 (s, 3H), 7.30 (s, 1H), 7.60-7.70 (m, 3H), 7.81 ( d, 1H), 7.94 (s, 1H).
  • Compound A-70 1 H-NMR (400MHz, CDCl 3 ): ⁇ 3.02 (s, 3H), 3.54 (s, 3H), 3.76 (s, 3H), 6.86-6.96 (m, 1H), 7.15 ( s, 1H), 7.50-7.82 (m, 4H).
  • Compound A-71 1 H-NMR (400MHz, CDCl 3 ): ⁇ 1.45 (t, 3H), 3.20 (q, 2H), 3.35 (s, 3H), 3.48 (s, 3H), 3.65 (s, 3H), 4.98-5.85 (m, 1H), 7.25 (s, 1H), 7.79 (d, 1H), 8.12 (d, 1H).
  • Compound A-74 1 H-NMR (400MHz, CDCl 3 ): ⁇ 3.19-3.30 (m, 4H), 3.52 (s, 3H), 3.69-3.79 (m, 7H), 7.25 (s, 1H), 7.92-8.09 (m, 3H).
  • Compound A-75 1 H-NMR (400MHz, CDCl 3 ): ⁇ 3.13 (s, 3H), 3.51 (s, 3H), 3.78 (s, 3H), 7.20 (s, 1H), 7.59 (dd, 1H), 7.86 (d, 1H), 7.89 (d, 1H).
  • Compound B-2 1 H-NMR (400MHz, CDCl 3 ): ⁇ 2.49-2.63 (m, 2H), 2.80-2.89 (m, 1H), 3.09-3.18 (m, 1H), 3.35-3.40 (m, 1H), 3.55 (s, 3H), 3.69-3.73 (m, 1H), 4.07-4.16 (m, 2H), 4.29-4.34 (m, 1H), 4.61-4.68 (m, 1H), 7.19 (s, 1H), 7.60-7.99 (m, 6H).
  • Compound B-9 1 H-NMR (400MHz, CDCl 3 ): ⁇ 1.79 (m, 2H), 2.09-2.23 (m, 2H), 3.30-3.45 (m, 4H), 3.54 (s, 3H), 3.74 (s, 3H), 7.16 (s, 1H), 7.89 (s, 2H).
  • Compound B-11 1 H-NMR (400MHz, CDCl 3 ): ⁇ 2.15 (s, 3H), 2.50-2.78 (m, 5H), 3.41-3.56 (m, 5H), 3.69 (s, 3H), 4.12-4.28 (m, 4H), 7.13 (s, 1H), 7.49 (s, 1H).
  • Compound B-12 1 H-NMR (400MHz, CDCl 3 ): ⁇ 1.41 (s, 6H), 2.22-2.40 (m, 4H), 2.56 (s, 3H), 3.39-3.45 (m, 2H), 3.51 (s, 3H), 3.68 (s, 3H), 7.15 (s, 1H), 7.36 (d, 1H), 7.62 (d, 1H).
  • Compound B-13 1 H-NMR (400MHz, CDCl 3 ): ⁇ 3.51 (s, 3H), 3.59 (dt, 2H), 3.73 (s, 3H), 4.83-4.95 (m, 2H), 7.18 ( s, 1H), 7.56 (d, 1H), 7.76 (d, 1H).
  • Test Example 1 (1) Preparation of test emulsion POA allylphenyl ether (4.1 parts by weight), POE-POP glycol (1 part by weight), POE sorbitan laurate (0.8 parts by weight), glycerin (2.6 parts by weight) , Dimethylformamide (65.9 parts by weight), N-methylpyrrolidone (5.1 parts by weight), cyclohexanone (15.4 parts by weight), and aromatic hydrocarbon (5.1 parts by weight) were mixed and dissolved. , Emulsion was prepared.
  • a 150 cm 2 pot is filled with soil, and the surface layer is covered with Enbaku (Avena sativa), Chamomile (Matricaria chamomilla), Setaria faberi (Setaria faberi), Digitaria ciliaris (Digitaria ciliaris), and Amaranthus retroflexus (Abutilon theophrasti). Amaranthus retroflexus) seeds were sown and lightly covered with soil.
  • A-1, A-2, A-3, A-4, A-5, A-6, A-9, A-10, and B-1 compounds should be applied in an amount of 1000 g per hectare. It was sprayed. As a result, all the compounds had a herbicidal rate of 80% or more with respect to velvetleaf.
  • the compounds of A-1, A-2, A-3, A-4, A-5, A-6, A-10, and B-1 were sprayed in an amount of 1000 g per hectare. As a result, all the compounds had a herbicidal rate of 80% or more with respect to chamomile.
  • the compounds shown in Table 5 were sprayed so as to have a spraying amount of 250 g per hectare. As a result, all the compounds showed 80% or more herbicidal activity against velvetleaf.
  • the compounds shown in Table 7 were sprayed so as to have a spraying amount of 250 g per hectare. As a result, all the compounds showed 80% or more herbicidal activity against chamomile.
  • the compounds shown in Table 9 were sprayed so as to have a spraying amount of 250 g per hectare. As a result, all the compounds showed 80% or more herbicidal activity against embaku.
  • the compounds shown in Table 11 were sprayed so as to have a spraying amount of 250 g per hectare. As a result, all the compounds showed 80% or more herbicidal activity against Setaria faberi.
  • the compounds shown in Table 13 were sprayed so as to have a spraying amount of 250 g per hectare. As a result, all the compounds showed 80% or more herbicidal activity against crabgrass.
  • the compounds shown in Table 15 were sprayed so as to have a spraying amount of 250 g per hectare. As a result, all the compounds showed 80% or more herbicidal activity against Amaranthus retroflexa.
  • the compounds of the present invention may be compounds having a high herbicidal effect, including compounds that could not be exemplified. It can be understood.
  • New 7-oxa-3,4-diazabicyclo [4.1.] Useful as an active ingredient of herbicides, which has a reliable weed control effect even at a low dose, has less phytotoxicity to crops, and is highly safe for the environment. 0] Hepta-4-en-2-one compounds and herbicides can be provided.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Plant Pathology (AREA)
  • Environmental Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Dentistry (AREA)
  • Agronomy & Crop Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
PCT/JP2020/035689 2019-09-25 2020-09-23 ７－オキサ－３，４－ジアザビシクロ［４．１．０］ヘプタ－４－エン－２－オン化合物および除草剤 WO2021060240A1 (ja)

Priority Applications (14)

Application Number Priority Date Filing Date Title
CA3153862A CA3153862A1 (en) 2019-09-25 2020-09-23 7-oxa-3,4-diazabicyclo [4.1.0] hept-4-en-2-one compound and herbicide
MX2022002898A MX2022002898A (es) 2019-09-25 2020-09-23 Compuesto de 7-oxa-3,4-diazabiciclo-[4.1.0]-4-hepten-2-ona y herbicida.
UAA202200941A UA128513C2 (uk) 2019-09-25 2020-09-23 7-окса-3,4-діазабіцикло[4.1.0]гепт-4-ен-2-он і гербіцид
JP2021548911A JP7459122B2 (ja) 2019-09-25 2020-09-23 ７－オキサ－３，４－ジアザビシクロ［４．１．０］ヘプタ－４－エン－２－オン化合物および除草剤
PL20870221.7T PL4035528T3 (pl) 2019-09-25 2020-09-23 Związek 7-oksa-3,4-diazabicyklo[4.1.0]hept-4-en-2-onowy i herbicyd
CN202080063624.1A CN114375292A (zh) 2019-09-25 2020-09-23 7－氧杂－3,4－二氮杂双环［4.1.0］庚－4－烯－2－酮化合物和除草剂
AU2020355994A AU2020355994A1 (en) 2019-09-25 2020-09-23 7-oxa-3,4-diazabicyclo[4.1.0]hepta-4-ene-2-one compound and herbicide
EP20870221.7A EP4035528B1 (en) 2019-09-25 2020-09-23 7-oxa-3,4-diazabicyclo[4.1.0]hept-4-en-2-one compound and herbicide
KR1020227007865A KR20220066885A (ko) 2019-09-25 2020-09-23 7-옥사-3,4-디아자비시클로[4.1.0]헵타-4-엔-2-온 화합물 및 제초제
ES20870221T ES2984558T3 (es) 2019-09-25 2020-09-23 Compuesto y herbicida de 7-oxa-3,4-diazabiciclo[4.1.0]hept-4-en-2-ona
BR112022003616A BR112022003616A2 (pt) 2019-09-25 2020-09-23 Composto, herbicida, e, método para controlar ervas daninhas monocotiledôneas e/ou dicotiledôneas
US17/636,710 US20220289758A1 (en) 2019-09-25 2020-09-23 7-oxa-3,4-diazabicyclo [4.1.0] hept-4-en-2-one compound and herbicide
DK20870221.7T DK4035528T3 (da) 2019-09-25 2020-09-23 7-oxa-3,4-diazabicyclo[4.1.0]hept-4-en-2-on-forbindelse og ukrudtsmiddel
ZA2022/02626A ZA202202626B (en) 2019-09-25 2022-03-03 7-oxa-3,4-diazabicyclo [4.1.0] hept-4-en-2-one compound and herbicide

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2019-174531 2019-09-25
JP2019174531 2019-09-25

Publications (1)

Publication Number Publication Date
WO2021060240A1 true WO2021060240A1 (ja) 2021-04-01

Family

ID=75165833

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2020/035689 WO2021060240A1 (ja) 2019-09-25 2020-09-23 ７－オキサ－３，４－ジアザビシクロ［４．１．０］ヘプタ－４－エン－２－オン化合物および除草剤

Country Status (18)

Country Link
US (1) US20220289758A1 (enrdf_load_stackoverflow)
EP (1) EP4035528B1 (enrdf_load_stackoverflow)
JP (1) JP7459122B2 (enrdf_load_stackoverflow)
KR (1) KR20220066885A (enrdf_load_stackoverflow)
CN (1) CN114375292A (enrdf_load_stackoverflow)
AU (1) AU2020355994A1 (enrdf_load_stackoverflow)
BR (1) BR112022003616A2 (enrdf_load_stackoverflow)
CA (1) CA3153862A1 (enrdf_load_stackoverflow)
DK (1) DK4035528T3 (enrdf_load_stackoverflow)
ES (1) ES2984558T3 (enrdf_load_stackoverflow)
HU (1) HUE067748T2 (enrdf_load_stackoverflow)
MX (1) MX2022002898A (enrdf_load_stackoverflow)
PL (1) PL4035528T3 (enrdf_load_stackoverflow)
PT (1) PT4035528T (enrdf_load_stackoverflow)
TW (1) TWI838583B (enrdf_load_stackoverflow)
UA (1) UA128513C2 (enrdf_load_stackoverflow)
WO (1) WO2021060240A1 (enrdf_load_stackoverflow)
ZA (1) ZA202202626B (enrdf_load_stackoverflow)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022196528A1 (ja) * 2021-03-19 2022-09-22 日本曹達株式会社 ７－オキサ－３，４－ジアザビシクロ［４．１．０］ヘプタ－４－エン－２－オン化合物および除草剤
WO2022202642A1 (ja) * 2021-03-22 2022-09-29 日本曹達株式会社 除草性組成物

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013050421A1 (en) 2011-10-04 2013-04-11 Syngenta Limited Herbicidal pyridazinone derivatives
JP2017518984A (ja) * 2014-05-21 2017-07-13 バイエル・クロップサイエンス・アクチェンゲゼルシャフト ５−（ヘテロ）アリール−ピリダジノン類及び除草剤としてのそれらの使用
JP2019174531A (ja) 2018-03-27 2019-10-10 株式会社ジャパンディスプレイ 表示装置

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0600507B1 (en) * 1992-12-04 1996-03-06 MITSUI TOATSU CHEMICALS, Inc. 3-Azabicyclo(3.1.0.)hexane-2-one derivatives and Herbicidal Compositions Containing them as Herbicidally Active Ingredients
PE20190408A1 (es) * 2016-03-30 2019-03-14 Ishihara Sangyo Kaisha Compuesto de piridazinona o su sal y herbicida que lo contiene
TWI785022B (zh) * 2017-03-28 2022-12-01 美商富曼西公司 新穎噠嗪酮類除草劑
AR124943A1 (es) * 2021-03-19 2023-05-24 Nippon Soda Co Compuesto 7-oxa-3,4-diazabiciclo[4.1.0]hept-4-en-2-ona y herbicida
AR125081A1 (es) * 2021-03-22 2023-06-07 Nippon Soda Co Composición herbicida

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013050421A1 (en) 2011-10-04 2013-04-11 Syngenta Limited Herbicidal pyridazinone derivatives
JP2014528960A (ja) * 2011-10-04 2014-10-30 シンジェンタ リミテッド 除草性ピリダジノン誘導体
JP2017518984A (ja) * 2014-05-21 2017-07-13 バイエル・クロップサイエンス・アクチェンゲゼルシャフト ５−（ヘテロ）アリール−ピリダジノン類及び除草剤としてのそれらの使用
JP2019174531A (ja) 2018-03-27 2019-10-10 株式会社ジャパンディスプレイ 表示装置

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022196528A1 (ja) * 2021-03-19 2022-09-22 日本曹達株式会社 ７－オキサ－３，４－ジアザビシクロ［４．１．０］ヘプタ－４－エン－２－オン化合物および除草剤
WO2022202642A1 (ja) * 2021-03-22 2022-09-29 日本曹達株式会社 除草性組成物

Also Published As

Publication number Publication date
BR112022003616A2 (pt) 2022-05-24
UA128513C2 (uk) 2024-07-31
CN114375292A (zh) 2022-04-19
HUE067748T2 (hu) 2024-11-28
MX2022002898A (es) 2022-04-06
AU2020355994A1 (en) 2022-03-17
US20220289758A1 (en) 2022-09-15
PT4035528T (pt) 2024-04-23
TWI838583B (zh) 2024-04-11
JP7459122B2 (ja) 2024-04-01
KR20220066885A (ko) 2022-05-24
EP4035528A1 (en) 2022-08-03
EP4035528B1 (en) 2024-03-27
DK4035528T3 (da) 2024-04-15
EP4035528A4 (en) 2023-03-01
PL4035528T3 (pl) 2024-07-08
ES2984558T3 (es) 2024-10-29
TW202126659A (zh) 2021-07-16
CA3153862A1 (en) 2021-04-01
JPWO2021060240A1 (enrdf_load_stackoverflow) 2021-04-01
ZA202202626B (en) 2023-12-20

Similar Documents

Publication Publication Date Title
JP7459122B2 (ja) ７－オキサ－３，４－ジアザビシクロ［４．１．０］ヘプタ－４－エン－２－オン化合物および除草剤
JP7675042B2 (ja) 除草性組成物
WO2022196528A1 (ja) ７－オキサ－３，４－ジアザビシクロ［４．１．０］ヘプタ－４－エン－２－オン化合物および除草剤
WO2021193410A1 (ja) ベンズアミド化合物および除草剤
JP7510428B2 (ja) ピリダジン化合物および除草剤
JP7535530B2 (ja) ピリダジン化合物および除草剤
RU2818255C2 (ru) 7-окса-3,4-диазабицикло[4.1.0]гепт-4-ен-2-оновое соединение и гербицид
RU2817020C2 (ru) Пиридазиновое соединение и гербицид
WO2020246418A1 (ja) ベンズアミド化合物および除草剤
WO2025114252A1 (de) Substituierte isophtalsäurediamide und ihre verwendung als herbizide

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 20870221

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 2021548911

Country of ref document: JP

Kind code of ref document: A

REG Reference to national code

Ref country code: BR

Ref legal event code: B01A

Ref document number: 112022003616

Country of ref document: BR

ENP Entry into the national phase

Ref document number: 3153862

Country of ref document: CA

ENP Entry into the national phase

Ref document number: 2020355994

Country of ref document: AU

Date of ref document: 20200923

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: DE

ENP Entry into the national phase

Ref document number: 2020870221

Country of ref document: EP

Effective date: 20220425

ENP Entry into the national phase

Ref document number: 112022003616

Country of ref document: BR

Kind code of ref document: A2

Effective date: 20220224